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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

Publication DOI: 10.1111/j.1432-1033.1971.tb01549.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Max-Planck-Institut fiir Immunbiologie, Freiburg i. Br., Statens Seruminstitut, Helsinki

In order to investigate the core structure of the lipopolysaccharide from an Escherichia coli 0100 strain, two derivatives were prepared from this strain by introducing genetic material from Salmonella abony. One, an SR hybrid, contained a lipopolysaccharide with short side chains consisting of simple repeating units of Salmonella group B specificity attached to the E. coli core. The other, an R form, contained only the E. coli core and no O side chains, due to a mutation in the Salmonella rfb chromosomal region, which determines the synthesis of the O repeating units. By partial acid hydrolysis of the SR and R lipopolysaccharides, oligosaccharide fragments were obtained which made it possible to reconstruct the hexose region of the core (see formula below). Methylation studies performed on the dephosphorylated polysaccharides confirmed and extended these results. It was found that only about 60% of the distal glucose units of the core chains were substituted by N-acetylglucosamine residues. Further, the heptose region was shown to form a branched trisaccharide. On mild acid hydrolysis of both lipopolysaccharide preparations a Gal-α1,7(8)-KDO disaccharide was formed, indicating that a galactose unit is linked to the 2-keto-3-deoxyoctonate (KDO) portion of the lipopolysaccharide. After Smith degradation of the SR lipopolysaccharide, the oligosaccharide Gal-β1,4-Glc-glycerol was identified which derived from the linkage region between the Salmonella type repeating unit and the E. coli core. Only the core stubs substituted by N-acetylglucosamine residues carried an O-specific unit. On the basis of the these findings the partial structure of the E. coli 0100 core polysaccharide with a Salmonella group B-specific unit attached to it is proposed as given below. The relationships to core structures identified in lipopolysaccharides of other representatives of Enterobacteriaceae are discussed.

Structure type: structural motif or average structure
Location inside paper: Fig. 5
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_130670,IEDB_130693,IEDB_133751,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150901,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_983931,SB_192,SB_7

Methods: methylation, GLC-MS, partial acid hydrolysis, sugar analysis, dephosphorylation, GLC, mild acid hydrolysis, Smith degradation, enzymatic degradation, paper chromatography, paper electrophoresis
Comments, role: tentative structure; one side chain LDmanHep may be missing; localization of PEtN is unclear between LDmanHep and KDO

Related record ID(s): 122390
NCBI Taxonomy refs (TaxIDs): 2067420
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There are 144 chemically distinct structures. Please, select:

CC(=O)N[C@H]1[C@@H](O[C@H]2[C@@H](O[C@H]3[C@@H](O[C@@H]4[C@@H](O)[C@@H](O[C@@H]5[C@H](O)[C@@H](O[C@@H]6[C@H](O)[C@@H](O[C@H]7[C@@H]([C@H](O)CO)OC(OC(=O)C8(OC(=O)C9(O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O9)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO[C@H]9O[C@H](CO)[C@H](O)[C@H](O)[C@H]9O)O8)(C(=O)O)C[C@H]7O)O[C@H]([C@@H](O)CO[C@H]7O[C@H]([C@@H](O)COP(=O)(O)OP(=O)(O)OCCN)[C@@H](O)[C@H](O)[C@@H]7O)[C@H]6OP(=O)(O)OP(=O)(O)OCCN)O[C@H]([C@@H](O)CO[C@H]6O[C@H]([C@@H](O)COP(=O)(O)OP(=O)(O)OCCN)[C@@H](O)[C@H](O)[C@@H]6O)[C@H]5OP(=O)(O)OP(=O)(O)OCCN)O[C@H](CO[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize